I love Sydney. Not everyone does, or will, but I suspect that the love/hate relationship will be the same as it is for San Francisco: you either love it or you hate it. But whatever you do, give it a chance! If you’ve gone all that way, don’t just say “I don’t want to go to Sydney” but, rather, suck it up and experience a truly multi-cultural – and wonderful – city!
I’m afraid that hotel recommendations are pretty hard to come by. This is, in part, due to the fact that Sydney – and Australia in general – are really quite pricey. My best advice, until I find a place that I can unequivocally recommend, is to search online for the best deal and use your best judgment.
On my last trip, I stayed at the Grace Hotel. It was okay but I honestly wouldn’t recommend you stay here. The staff are great, but the price for what you get, is not worth it.
For a special night out – date, friends, family, or just your own personal celebration – I highly recommend Pendolino (http://www.pendolino.com.au/). This newly opened restaurant is in The Strand shopping arcade but don’t let this put you off. The food is amazing, the wine outstanding, and the decor really nice. While i was here, there were people on dates, family outings, a few business meals and a couple of people eating on their own. Come one, come all I say!
Another outstanding restaurant in the CBD is pony bar and restaurant (http://www.ponydining.com.au/) in the rocks. Oh my, this place is amazing! It is small, so be sure to book a table, and if the weather is nice, ask to sit outside. But if you are inside, fear not: the open kitchen and smell of wood-fired grill will calm you and entice your senses. I would return right now if I could!
If you are in search of a vegetarian restaurant, I can recommend two. The first that I would recommend which, I bet, would be amazing in the summer is Bodhi (http://www.bodhi.id.au/). I found the service a little rushed but the food was amazing. They had a bit of mock-meat and other delights that could keep you coming back day after day.
But, rather than keep returning to the same restaurant, hop on the train to Newtown. (Ask at your hotel, it’s easy to get there and cheap!) Newtown has the requisite cool factor: tats, piercings, galleries, and bars everywhere. And an amazing vegetarian restaurant called the Green Gourmet (http://www.greengourmet.com.au/). Don’t be put off by the website or even the look of the place – both are a bit tired – because the food is amazing! There is also buffet that you can pay by the weight for, but just order a la carte. The only downside: they have no alcohol or green tea so turn a blind eye, have a soda or some fancy tea, sit back, and relax. Oh yeah: and the staff are wonderful and really helpful with advice and suggestions. Love this place!
And lastly, if you are in Sydney for a convention (although the convention center is being rebuilt and thus closed until 2015 I think), Zaaffran (http://www.zaaffran.com/) in Darling Harbour is probably some of the best Indian food I’ve had in a long time. I won’t tell you the number of times I was here but I can tell you that, it is easy to get a table at lunch but for dinner, be sure to have a ressie or you will be waiting! And yes, the views of Darling Harbour at night are incredible!
Beyond the standard recommendations that any tour book will provide, I would encourage you to make your way to as many beaches along the coast as you can. If you have a friend, buy them petrol and dinner and ask them to drive you around. You will see things and people that you won’t see in the CBD.
And when you are out and about, make your way to the Vaucluse House (http://www.vauclusehousetearooms.com.au/our-venues/vaucluse-house/home). What a gorgeous little park with an amazing tea room that serves brunch and lunch. Even in the winter, there was a wedding and reception taking place so don’t be surprised if you need to wait a bit. It is worth it!